Matchmakers, before you hang the mistletoe ...

A common-sense guide to setting up friends and relatives during the holidays

November 21, 2012|By Nara Schoenberg, Tribune Newspapers

(Jill Fromer, Getty Images)

When Victorya Michaels Rogers was single, a friend set her up with three men. The first was great, and they dated on and off for a year. The second was wonderful, but, at 23, a tad young for Rogers, then 30.

The third was an out-of-town businessman Rogers' friend met at the Golden Globes. Rogers' friend and the businessman chatted in the lobby and hit it off, and, on a hunch, the friend introduced him to Rogers. When the man came back into town he looked up the two women, and they all went out to lunch. The next night, when he joined them again, this time for an outing with their friends, it was clear that the friend's instinct had been correct: Rogers was entranced.

"She's going to marry him — just watch," Rogers' friend predicted, correctly, that very night.

In the season of mistletoe and champagne flutes, when visions of chemistry and compatibility dance through aspiring matchmakers' heads, it's only natural to want to bring great people together, and dating experts say that singles in search of a serious relationship generally appreciate a thoughtful and tactful setup.

The key, though, is thoughtful and tactful. Just about anyone who has ever dated can tell you about a blind date that never, ever should have happened. And, for the unattached, the holidays are often already a time of unwelcome attention, according to Megan Carson, author of "A Year of Blind Dates: A Single Girl's Search for 'The One' " (Regal).

"(You think), 'Oh gosh, I'm by myself, and I have to go to the family dinner, and Uncle Steve is going to ask me for the 100th time why I'm not married yet,'" Carson says. "Often we're already sensitive, so if you can just find a fun and casual way to connect people I recommend that. Just kind of allow it to happen organically after you make the initial introduction."

Among her recommendations: Keep the hype ("I know he's the one for you!") to a minimum and don't send people off on blind dates.

Carson, who met her current boyfriend through her pastor, recommends having a party or inviting a group of people to a restaurant, bar or concert where introductions can be made without major fanfare.

Rogers, author of "Finding a Man Worth Keeping: 10 Dating Secrets That Work" (Howard Books), favors the group meeting as well. When you introduce the pair, mention a common interest, she says ("I know you both like to ski") and then stick around, if need be, to get the dialogue going. It's hard enough to meet somebody new and just start chatting, Rogers says, and the problem is compounded when you throw romantic chemistry into the equation.

Setups can be great, Rogers and Carson agree, but not all setups are created equal.

"Matchmaking is the art of knowing what matters most (to people) and if they'll have enough in common," Rogers says. "You want to know enough about each side to know if they're going to get along."

Among the factors you may want to consider: common interests, compatible personalities, life goals and values.

Looks count very much to some people, Rogers says, and you're not doing your pretty but not-gorgeous gal pal a favor if you set her up with a man who only dates women who look like models.

In one unfortunate case, Rogers recalls, a well-meaning relative arranged for her to meet a successful, good-looking man, who came to her workplace and took her to lunch.

"I didn't even make it to the car in the parking structure before I knew about his obsession with guns," Rogers says.

The gun talk continued during an uncomfortable lunch in which her date spoke bitterly of his disappointment with himself over his choice, 20 years before, to go to Canada and avoid the draft. He was horrified when Rogers implied that her relative had told them a little about each other: "I told you, I didn't know anything about you!"

Lauren Kitchens-Steward, a radio host who reunited two old friends who subsequently married, says the two had similar easygoing, fun-loving personalities and "really clicked."

When Rogers talks about great matchmaking, she talks about the friend who introduced her to her husband.

"She had odd quirks, but she 'got' people and she focused on the person," Rogers says of her friend. "She always focused on what the guy was into and personality, and that is the key. You listen to what people are looking for and what they like and don't like. You don't always put the pretty people together — it's who is compatible."

Matchmaking don'ts

Never lie. If a guy isn't conventionally handsome and you say he is, that will lead to a really awkward first meeting — even if looks aren't super-important to either party.

Don't facilitate one-night stands. Don't set up a friend who's looking for love with a confirmed womanizer (or the female equivalent). That's not fair to anyone.

Don't set up a stranger. Try to spend some time with an appealing acquaintance before you set them up with a friend. That way you can at least get some sense of whether your prospect is a total jerk or an unrepentant gold digger.